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I know this is a bit atypical for what I generally come to this sub-forum for, but it seemed like to right place to get potential ideas for a project I'm considering.

I regularly have a need/want for a speaker/system portable enough to at least easily bring outside, and more ideally able to fit in my car. Not much of the work I've done with mid-high end home audio, nor that which I do with pro audio equipment seems very relevant in finding something that suits my needs. At present this this simple TDK boombox is actually kindof impressive given what it is and the fact I picked it up for $70 on w00t, But I'm wondering if I could build something to better suit the settings I use it in, generally at small-medium parties in a decent sized room or spread out around a rather large pool.

Before I moved, the setup I used outdoors was just a pair of the fairly cheap HTD outdoor speakers connected as my main indoor setup's second zone, and I was more than happy with it on a 500 sq. ft. roof deck (smaller than what I'm usually dealing with now.) Obviously the advantage to any properly spaced stereo sound in such a setting is the ability to fill the area with sound at reasonable volumes, compared to having to blast audio from a single source which makes being anywhere near it intolerably loud for the sake of audibility at the furthest points. Three potential options that seemed temporarily adequate came to mind to deal with this AND meet my new need of portability: using powered speakers for the sake of eliminating the need for an amplifier and cutting cables down to just two long 1/4" connected to a 2x1/4"->3.5mm adapter (I currently bring out my Mackie HR624 II studio monitors for larger outdoor parties at my home), using a portable PA system like the Fender Passport 150 which adds size with the mixer, but breaks down into an incredibly portable package, and adds some welcome though unecessary versatility to source options (including mics for karaoke use), and lastly I considered the possibility of looking into a way of using powered speakers but somehow rigging them to use the same source wirelessly; this would create the most portable solution and remove the risk inherent in running long cables in an environment with a large number of people who are probably drinking. I think i'd lose it if someone ever toppled one of my studio monitors.

Not everyone is going to want to read all that so I'm going to also break down desired factors in a potential scenario in which I'd want to use the setup I'm looking to buy or build:
-800 sq. ft. outdoors by a pool, or 500-600 sq. ft. in a large living room as the setting
-Small enough to easily fit in the trunk or back seat of a sedan
-Audibility throughout the setting without creating large areas of deafening sound by the actual speakers
-Ability to play from 3.5mm and RCA sources
-Quick set up and break down
-Limited cables (ideally little more than the power cables for powered speakers or a small amplifier mounted to the back of a speaker/on a stand)
Not necessary but desirable:
-Some degree of durability (though I suppose any speaker can be modified for this

Important:
- Having two separated speakers is something I'd LIKE to avoid but can't think of any other way to lessen the need to crank the sound just to reach far ends (especially outside) at a level that is at least audible.
- I've stated the ideal; I don't expect all of these things to be doable, but to at least improve upon what I'm currently using.
- I generally listen to FLAC run through my portable amp/DAC with my UE TripleFi 10s when portable, and almost strictly lossless from my HTPC -> DAC -> Receiver -> Aperion 5.1 setup in my bedroom. I don't expect quality that comes anywhere near either of these with something as portable as I'm describing. Most audio I have that isn't lossless is 320kbps, but if that sounds the exact same as content thats 192kbps on this I'd be completely fine with it.

Like I said these are IDEAL conditions, truthfully I started to consider the DIY route after being inspired by an article on lifehacker about turning one of those cheap multi-bulb lamps into a portable music player, here, turning the housing for two of the light sockets into housing for two cheap loudspeakers. Though it was pretty crudely done, I like the idea because it eliminates the necessity for a stand, cabling can be routed inside the lamp post, and mounting a small stand (in his case an altoids box) onto the center could easily hold a mini amp and any portable audio player without adding much bulk. Though not as effective as using stereo speakers, I feel like if properly done, a similar design might suit my needs, potentially using three speakers from parts express, reworking and modifying the enclosures quite a bit (or just replacing them while trying to keep the design somewhat similar), and a mini amp.

I'm very new to DIY audio, but have been reading this sub-forum for over a year now, and hope to build my own towers soon, that being more in my element, so sorry in advance if I'm making any poor assumptions/generally approaching this illogically. Thanks for your help.

You're definitely going to have to get creative here, one of the best things about DIY. I would start with a sub box, maybe featuring a 12" tuned in the 30-50hz range in order to keep the box very small. You can then build the mixer and all of the amps into the back of the sub box in their own separate section. A couple of compact PA tops could then be setup and wired from the subs , or you could just have a single top on a pole mount above the sub if you want to stick with a single location. Or maybe even have two pole mounts from the sub at a V angle in order to get some spread from a single point?